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4-Methylmorpholine → [4-(2,4-Dimethylphenyl)-[1,4]diazepan-1-yl][4-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanone

HRID 2411477
Notes
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Reaction equation

HRID 2411477 reaction equation
[O:1]=[S:2]1(=[O:16])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1.Cl.[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=1[N:26]1[CH2:32][CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.CN1CCOCC1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>CO.O1CCOCC1.O>[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=1[N:26]1[CH2:32][CH2:31][CH2:30][N:29]([C:11]([C:10]2[CH:9]=[CH:8][C:7]([N:3]3[CH2:4][CH2:5][CH2:6][S:2]3(=[O:1])=[O:16])=[CH:15][CH:14]=2)=[O:13])[CH2:28][CH2:27]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 66250114-(1,1-Dioxo-1,2-thiazolidin-2-yl)benzoic acidHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 673808831-(2,4-Dimethylphenyl)-[1,4]diazepane hydrochloride

Product 1

HCID 71252897[4-(2,4-Dimethylphenyl)-[1,4]diazepan-1-yl][4-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanone
Yield 49.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)benzoic acid (253 mg) described in Preparation Example 16, 1-(2,4-dimethylphenyl)-[1,4]diazepane hydrochloride (253 mg) described in Preparation Example 93 and N-methylmorpholine (0.12 mL) was dissolved in a solution of methanol (2 mL), 1,4-dioxane (2 mL) and water (0.5 mL), 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (349 mg) was added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give the title compound (223 mg).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. customthe solvent was evaporated
  5. customThe obtained residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-32da236d9a4e49ac87a05a9c5fd562f3
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08816079B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes